I noticed on the voltage regulator picture that the wire loom is coming up in front of the generator. I believe the correct routing is the wire loom coming up behind the generator. It seems to me that if the the generator or even the voltage regulator were removed at some time it could have been an easy mistake to replace them with the wire loom in front. As Jim mentioned Harley did a good job at hiding most of the wiring. Coming up behind the generator would keep it out of the way and reduce the risk of getting it snagged on something.
Pictures are of the 1954 KH factory photo HD-20061, an original paint 1952 K and my 1953 KK. I noticed looking through the gallery there are several examples of restored bikes that have the loom coming up in front but restored machines are not to be taken as proof. I only submit a picture of my '53KK not as proof but rather a good picture of what I believe it should look like. The factory photo and the OP '52 pictures are pretty solid evidence of how the routing should be.
Stan